4-(Chlorosulfonyl)-2-hydroxybenzoic acid → HCID 9960530, compound

HRID 1954264Notes

Reaction equation

HRID 1954264 reaction equation
[Br:1][C:2]1[C:11]2[S:12][C:13]([CH3:16])=[C:14]([CH3:15])[C:10]=2[C:9]([C:17]2[CH:22]=[C:21]([CH3:23])[C:20]([OH:24])=[C:19]([CH3:25])[CH:18]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.Cl[S:27]([C:30]1[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[C:32]([OH:39])[CH:31]=1)(=[O:29])=[O:28]>>[Br:1][C:2]1[C:11]2[S:12][C:13]([CH3:16])=[C:14]([CH3:15])[C:10]=2[C:9]([C:17]2[CH:22]=[C:21]([CH3:23])[C:20]([O:24][S:27]([C:30]3[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[C:32]([OH:39])[CH:31]=3)(=[O:29])=[O:28])=[C:19]([CH3:25])[CH:18]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2

Participants

3

Reactant 2

HCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acidHCID 18430706HCID 18430706, compound

Product 1

HCID 9960530HCID 9960530, compound

Procedure

Using 4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-dimethyl-phenol (0.302 g, 0.744 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (1.09 g, 4.61 mmol) the title compound was prepared according to the procedure in Example 1, step 9. Purification on Dynamax C18 eluting with 85% CH3CN/H2O (0.1% TFA added) gave 0.20 g (44%) of the title compound as a yellow solid, mp >225° C.; 1H NMR (DMSO-d6) δ 1.59 (s, 3 H), 2.16 (s, 6 H), 2.45 (s, 3 H), 7.19 (S, 2 H), 7.46-7.52 (m, 4 H), 7.65-7.69 (m, 1 H), 8.07 (d, 1 H), 8.21 (d, 1 H). IR (KBr) 3450, 2900, 1675, 1385 and 1185 cm-1. mass spectrum (-ESI), m/z 609/611 (M-H). Anal. Calcd. for C29H23BrO6S2.0.7H2O: C, 55.81; H, 3.94 N, 0.00. Found: C, 55.93; H, 4.23 N, 0.12.

Sources & evidence

ORD record
ord-853840d5820c4372bf0e88c0155f85c4
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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